In the 2005 Andy Garcia film “Lost City” you see social Havana at the height of its Hemingway-era glamour and glory. Fancy cars roaming clean streets, glittering people sipping cocktails in ritzy nightclubs, and the US gangstahs who made it all happen in cahoots with Fulgencio Batista, the last dictator.

Fidel and the revolution changed all that, and 60-plus years later under what turned out to be a replacement repressive dictatorship, Havana is a study in contrasts. It's a fascinating place: 40's and 50's classic American cars in bright colors rumbling along the sea-splashed Malecon and bouncing through rutted, potholed streets lined with Spanish colonial, baroque, and art deco style buildings some of which are brightly painted and restored, but most of which show exteriors of ravaged peeling paint, and many have dark, hollow-eyed glass-less window openings evoking nothing so much as Beirut after the bombing. Rusted balconies backed by crooked wooden shutters sport ragged laundry flapping languidly in the small breeze. Shoeless, shirtless kids kick a lumpy soccer ball between the curbs; wizened old fellows sit on stoops with the stub of a cigar jutting in their jaws, dark-skinned beauties in short shorts and tank tops saunter arm in arm and bicycle rickshaws cruise languidly looking for a tourist fare.

Cuba has been reasonably difficult for Americans to visit in the past due to the 60-year embargo, but last year the US government loosened things somewhat, through the re-introduction of a type of permit called the person-to-person license. The primary requirement for these licenses is that the tours include "meaningful interaction" with Cuban people. Itineraries for such never mention tourism, vacation, or beaches and scuba diving. Ours contained phrases like “a detailed explanation of events leading up to the revolution”; “meet with students and professors to learn about current artistic movements in Cuba” and “visit a community project that serves at-risk children and seniors”.

This tour is organized by the Cross-Cultural Journeys Foundation, and very luckily for us has only six travelers in total, hailing from New York, the Bay Area and Cincinnati. Thirty-two year old Adam Vaught, who has spent his adult life travelling and leading tours around the globe is CCJF’s “man in Cuba” and our tour director. Cuban guide Rafael and driver Roghelio complete our entourage. A comfortable 12-seat Mercedes van serves as our transport for the trip. The first cultural exchange program in which we participate is a program organized through La Iglesia de Merced in one of the barrios in old Havana by two Cubans who grew up in the barrio, Oscar and Ramon. With meager donated funds they are providing breakfast for four dozen of the local areas most needy children, and breakfast, lunch and a place to congregate for 60 or so of the barrio’s oldsters. All of our tour members have brought ibuprofen, vitamins, first aid kits, art materials, clothing or other “humanitarian supplies” to donate to Oscar’s and several other groups over the short course of the tour.

Our hotel, the Telegrafo sits adjacent to the Parque Central and the head of the broad poplar-lined esplanade of the Prado, at the edge of Havana Vieja. A UNESCO World Heritage Site, Havana Vieja encompasses an area of roughly 12 blocks by 20 on the harbor, or eastern side of the Prado. The Heritage area contains approximately 4000 buildings in a variety of styles including Neo-classical, colonial, Spanish baroque, Beaux Arts, and Moorish. Much historic preservation has been undertaken since the 90’s, and as a result many of the streets in the central area of old Havana have been renovated, the buildings sporting bright colors and cleaned beige stone, the streets smoothly cobbled. Elaine, an architect with the City Historian’s Office leads our group on a walking tour from the Capitolio—built in 1929 in an attempt to emulate the Capitol in Washington—down Brasil street, past several examples of successful renovations, to the Plaza Vieja, which is surrounded by stately restored historic buildings. The City Historian’s Department of Architecture developed a model in 1993 whereby the government granted seed capital to Habaguanex, a company set up for the purpose, and the right to income from buildings within Havana Vieja, with the proviso that all proceeds be reinvested. Their basic plan reinvests 45% of all revenue into renovation and restoration in Havana Vieja; 35% goes towards meeting the social needs of the neighborhood, and the balance helps fund historic renovation projects in other parts of the city. About a third of the buildings in Old Havana have been renovated or restored at this point. There are examples on every block of dilapidated buildings or mere facades that need restoration. Elaine estimates that a collapse or partial collapse of a building occurs in the area on a weekly basis.

Elaine leads us to the Plaza de San Francisco on which is located the church and convent of San Francisco de Asis originally constructed in 1608, and the elegant white marble Fuente de los Leones. The harbor is directly east, and on the north side sits the renovated neoclassical Loma del Comercio, built in 1907 as the stock exchange. From there we meander, sticking to the shade of the historic buildings in the spiking heat, along Calle Oficios to the Plaza de Armas, whose central garden is a bird-filled jungle draped with white, salmon and fuchsia bougainvilla. Armas is surrounded by the Palacio de los Capitanes Generales, Templete, a small neoclassic building, the Historic Post Office and the Hotel Santa Isabela, originally the 14th century palace of a Spanish noble family, where Jimmy Carter stayed and where as it turns out we will have our last night. A few more blocks bring us to the Plaza de la Catedral, fronted by the intensely baroque San Cristobal Catedral. Elaine wraps up her tour here, and we file into Hostal Conde de Villanueva for lunch of the usual choices of chicken, fish or pork, grilled and served with rice and black beans, preceded by a cucumber onion and tomato salad. Tasty enough, but as Adam said most accurately our first day "you don't come to Cuba for the food”.

The next morning we visit the Museo de Belles Artes to acquaint ourselves with important Cuban art from the 1800’s through the present. Earlier works are very much in a European style, but starting in the teens and twenties, artists such as Eduardo Abela and Fidelio Ponce de León developed a definitive Cuban style. Perhaps most iconic of those is René Portocarrero, whose thick layers of vibrant colors and intense detail seem to embody Havana.

In the afternoon we visit the ISA, Instituto Superior de Artes in the relatively upscale Miramar suberb, located on the site of a former country club. We’re guided by Professor Os Raggi (who looks quite young to be a professor), and meet several students in their studios working on paintings, prints, etchings and sculpture, all frantically getting ready for the Havana Biennale, which was to start the following week. Some terrifically innovative and interesting art is being produced here. We’re lucky to find a small and delightful acrylic Havana street-scene by Eduardo Solles to add to our collection of miniature landscapes and cityscapes. In addition to teaching at ISA, Os and his girlfriend Lorena founded and have been managing the Coco Project, which teaches art to disadvantaged children, and he heartily welcomes the art supplies which our group has brought for his kids.

For decades all restaurants, as well as hotels in Cuba were government owned and run, and tend toward simple and fairly uninteresting food. In recent years the government permitted families to acquire licenses to run private restaurants called paladares. These are family run businesses, almost always small and usually located in someone’s home. We tried two of these on “free nights” from the tour. La Guarida is one of the oldest, and some say the best paladar in Havana. Located in a half-demolished building in a dilapidated part of Centro Havana, one climbs two flights of stairs through crumbling, windowless floors to reach La Guarida. The actual restaurant is a pretty series of rooms with eclectic furnishings and walls covered in old photos and signed celebrity headshots. An herbed –anchovy mayonnaise comes with a basket of mixed bread to accompany our drinks. We share Piquillo peppers stuffed with tuna as a first course which is quite good. Grilled pork chops for Troy turn out to be somewhat dry and overcooked, but the eggplant and tomato ‘tart’ accompanied by a peppery cress salad that I choose is flavorful and delicious.

Music is everywhere in Cuba and Havana, and it’s almost all very good. Every restaurant and every hotel seems to have a house group. At night, walking the streets there are At lunch one day there is a trio of young ladies playing ballads and classical pieces on alto and tenor clarinet and bassoon.. At another there is a guitar duo playing flamenco. A sax and keyboard duet play every morning in our hotel restaurant for breakfast, no less! There are salsa bands and jazz combos, but the bulk of groups play the traditional Cuban Son, with its driving beat and country peasant lyrics re-popularized by the Buena Vista Social Club.

Two nights later finds us at La Terraza, located two blocks from our hotel in a building owned by the Spanish Sociedad Cultural Asturiana on the top floor terrace. Chef Jorge Ochoa works with one assistant at a large open charcoal grill, which permeates the terrace with wood smoke. Eggplant seems to be dear to the Cubans, and we start with slices of it wrapped around small sausages and cheese, secured with toothpicks and charred on the grill—a really delicious dish. Troy chooses lobster, which is enormous, if a bit overcooked again. Centered on my plate is a beautiful entire small grilled octopus which is tender, rich, and redolent of the sea. A side dish of grilled onions, zucchini, tomatoes, and peppers is great, but there is way too much of everything.

Our fifth day we hit the road for the south, and the colonial town of Trinidad. Most of a days drive takes us southeast through citrus groves, cane fields and banana plantations, skirting along the edge of the Ensenada de la Broa to The Bay of Pigs and the Playa Gironde, site of the abortive CIA-backed attempt to overthrow Castro in 1961. There is a small museum that chronicles the battle from the Cuban government point of view, and the English translations show the propaganda ministry in full bombastic and revolutionary throat. An hour east is the French-settled colonial seaside town of Cienfuegos. Known as the pearl of the sea, the architecture clearly shows a different influence than Havana. Rafa says that it's his favorite town in Cuba, but we find it somehow less interesting. Another hour winding and bouncing generally eastward brings so to the quite lovely town of Trinidad.

A logical second venue to visit after Havana, colonial Trinidad is a well preserved pastiche of curving cobbled streets and vibrant Caribbean pastels sitting below the rugged pine and eucalyptus-forested peaks of the Sierra de Escambray. Imposing two story mansions demonstrating the wealth of the slave owning sugar planters of the 17 and 1800's surround the central Plaza Mayor with its manicured shrubbery, black cast iron street lamps and green and white ceramic urns. Many of these are now museums--Colonial, Romantic, Archaeological, Architecture--the latter is particularly interesting. The streets surrounding the plaza are one story mottled tile roofed houses in canary, gold, ochre, dusty rose, acid green and that singularly intense Caribbean blue. The town is reminiscent of both San Miguel de Allende in Mexico, and Antigua Guatemala. In common with the latter, Trinidad has been declared a UNESCO world heritage site, and the traffic-free central area is lovingly preserved.

A block and a half west on the Calle Martinez Villena is La Canchanchara, a long narrow arcaded bar that serves a local drink called Canchancha--a beverage both smooth and strong made with aguardiente, honey, lime, water and ice. There are dark wood benches facing each other the length of the shaded patio, and a dozen or so locals are arguing at the top of their range about national baseball, gesticulating with cigars and the squat clay cups that bring the chanchancha. At the end of the bar, the band Son Trinitario blasts out a driving beat. Like Havana, music is ubiquitous in Trinidad-mostly traditional Cuban Son, and salsa.

Twenty minutes northeast of Trinidad lies the fertile Valle de Los ingenios, which means sugar mill--vast tracts of sugar plantations that were the source of so much 19th century Cuban wealth. Swaths of vibrant green cane snaked through by lines of royal palms backed by the Escambray peaks provide a magnificent view from an overlook. Descending to the valley, a short visit to the Manac Iznaga estate gives us sense of plantation life in the era, and a refreshing and delicious glass of celadon-green guarapo--fresh pressed cane juice to mitigate the beating midday heat.

Most restaurants in Trinidad have a house band for lunch and dinner, as does the paladar Sol y Son where we dine on our last night. After dinner, we wander to the open air Casa de Musica where bands fill the steps next to the Iglesias de Santisima Trinidad with locals and visitors dancing or swaying to the hypnotic rhythm. A couple of last shots of Havana Club 7 as we salsa in place absorbing the scene insure we won’t have any trouble getting a sound sleep our last night on this island of contrasts.